The action of perphthalic acid on 5-dihydroergosteryl and ergosteryl acetates

Alt, G. H.; Barton, Derek H. R.

doi:10.1039/jr9540001356

Cited by 22 publications

(9 citation statements)

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“…All known compounds (7-24) were identified by comparison of their chromatographic behavior, and their MS and 1 H-NMR data with those of the authentic samples (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) 33 (3H, s, H 3 -18), 2.55 (1H, m, H-20), 2.84 (2H, m, H-1a, H-4a 3H, s, H 3 -18), 1.14 (3H, s, H 3 -29), 1.23 (3H, s, H 3 -19), 1.24 (1H, m, H-15a), 1.25 (3H, s, H 3 -28), 1.35 (3H, s, H 3 -30), 1.50 (3H, s, H 3 -27), 1.52 (1H, m, H-16b), 1.53 (3H, s, H 3 -26), 1.63 (3H, m, H 2 -6, H-20), 1.76 (1H, m, H-15b), 1.83 (1H, m, H-22a C-NMR (100 MHz, CD 3 OD): see Table 1.…”

Section: Nudamentioning

confidence: 99%

“…In a continuation of our investigation of the chemical constituents from mushrooms, we describe here the isolation and structural elucidation of three new sterols, 5a,9a-epidioxy-(22E)-ergosta-7,22-diene3b ,6a -diol (1), 5a ,9a -epidioxy-(22E)-ergosta-7,22-diene3b ,6b -diol (2) and 3b ,5a ,9a ,14b -tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and three new triterpenoids, sublateriols A-C (4-6), as well as eighteen known compounds, (22E)-ergosta-5,7,9(11),22-tetraen-3b-ol (7), 2c,5) ergosterol (8), 2f,6) (22E)-ergosta-5,8,22-trien-3b-ol (9), 2c,7) ergosta-5,7-dien-3b-ol (10), 2c,6) (22E)-ergosta-7,22-dien-3b-ol (11), 2c,8) ergost-7-en-3b-ol (12), 2c,6) 5a,8a-epidioxy-(22E)-ergosta-6,22-dien-3b-ol (13), 2a,9) 5a,6a:8a,9a-diepoxy-(22E)-ergost-22-ene-3b ,7a -diol (14), 2e) 5a ,9a -epidioxy-3b -hydroxy-(22E)-ergosta-7,22-dien-6-one (15), 2b) 3b,5a,9a,14a-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (16), 2b) 3b ,5a , 9a-trihydroxy-(22E)-ergosta-7,22-dien-6-one (17), 2a,10) 3b, 5a,9a-tetrahydroxyergost-7-en-6-one (18), 2b) (22E)-ergosta-7,22-diene-3b,5a,6b-triol (19), 2a,11) ergost-7-ene-3b,5a,6b-triol (20), 2b,12) (22E)-ergosta-7,22-diene-3b,5a,6a,9a-tetrol (21), 2b) (22E)-ergosta-7,22-diene-3b,5a,6b,9a-tetrol (22), 2a,10) fasciculol B (23) 13,14) and fasciculol C (24) 14,15) from four edible mushrooms, Panellus (P.) serotinus (PERS. : FR.)…”

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New Sterols and Triterpenoids from Four Edible Mushrooms.

et al. 2001

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Four edible mushrooms, Panellus serotinus, Lepista nuda, Tricholoma matsutake and Naematoloma sublateritium, have been investigated chemically. Two new sterols, 5a a,9a a-epidioxy-(22E)-ergosta-7,22-diene-3b b,6a a-diol (1) and 5a a,9a a-epidioxy-(22E)-ergosta-7,22-diene-3b b,6b b-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lepista nuda. A new sterol, 3b b,5a a,9a a,14b b-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and compound 2 have been isolated from Tricholoma matsutake. Three new triterpenoids, sublateriols A-C (4-6), have been isolated from Naematoloma sublateritium. The structures of the new compounds were elucidated on the basis of their spectral data.

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Section: Nudamentioning

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New Sterols and Triterpenoids from Four Edible Mushrooms.

et al. 2001

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“…From the combined a and b extracts after column chromatography and subsequent preparative thin layer chromatography, ethyl linoleate and cerevisterol (16,20) were isolated in addition to nine lactarane sesquiterpenes, six of which were new compounds. The nine sesquiterpenes were lactaral (1) (14,16), furo- scrobiculin A (2), furanether A (3) ( 16), furanether B (3,8-enantiofuranether A) (4), furoscrobiculin B (5), furoscrobiculin C (6), furoscrobiculin D (7), lactaroscrobiculide B (8) and furandiol (9a) (21).…”

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Fungal Metabolites. VIII: Structures of New Sesquiterpenes From Lactarius Scrobiculatus

Battaglia¹,

Bernardi²,

Mellerio³

et al. 1980

J. Nat. Prod.

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GIORGIO MELLERIO', GIOI-ASSI T-IDARI* and P.io~.i I-ITA-FISSI~ * ?Isfituto di Chiniica Organicci--ni;,ersita degli Studi-lCale W r a n i e l l i 10-27100 PaLmia (Italy) 3Centro del C-TR p e r lo Studio delle Sostanre Organiche .\htiirali-Politecnico-Piarra L e o m r d o do Ti'nci 32-20133 X i l a n o (Italjj ;iBsTR.icT.-From lots of Lncfarrzts scrobzciilnfus extracted in different B-ays, in addition to ethyl linoleate and cerevisterol, nine lactarane sesquiterpenes have been isolated. The main compounds are furanosesquiterpenes, namely: furoscrobiculins -4-D (2, S-i), furanethers 13 and 4) and the already known lactaral (l), and furandiol 19a). Furthermore a new sesquiterpene lactone with the CO group in 13, lactaroscrobiculide B (8), has been isolated. The structures were elucidated mainly by spectroscopic methods and by some chemical transformations. Stereochemistry of most sesquiterpenes has been determined.Recently (1-3) we isolated from Lactariids scrobiciilatzks some sesquiterpenes 11-ith the lactarane skeleton which is peculiar to most of the knon-n Russulaceae metabolites (4-1i). At present the only mushrooms of this family containing sesquiterpenes with a completely different skeleton are L. deliciosus (1s) (guaianes) and L. uzidzis (19) (drimanes).Sou-11-e report the structures of ne!\ lactarane sesquiterpenes which were isolated from a nen-lot of L. scrobiciilatus extracted in a different way than in the previous \I ork (2. 3). DISCCSSIOSL. scrobiczilatus is easily distinguished not only by the morphological aspects (yellow color, big size. wrobiculated stem, pungent taste, etc.), but also by the secreted milky juice, n-hich, for some reason not yet understood, turns quickly from n hite to yelloJv when it appears at the surface of the fruit-body. This color change could indicate enzymatic degradation reactions : therefore, in order to prevent and to check possible alterations in the sesquiterpene composition. n-e carried out extraction in three different nays:The frozen material \vas then minced under its solvent and. after being removed by filtration. it was homogenized in ethanol and ice to extract the more polar compounds.b) The freshly collected mushrooms nere cut and put in acetone. The material \vas norked up in a dry-box under a S? stream as in a). In this case, the color change in the juice seemed to be slon-er but n-as still noticeable.a) The fruit-bodies nere frozen in drj ice and acetone.c) The fruit-bodiei n ere cut without any precaution.

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“…Ergosterol has been assumed to be the major sterol of Basidiomycetes [23, 2.51. The others C2, sterols related to ergosterol (cerevisterol, ergosterol peroxide) are frequently obtained from wide a variety of fungi [2,3,4,81. Several investigators suggested that these sterols were an artefact (oxydation products) of experimental procedures [I, 221. In N. fasciculare fruitbodies; ergosterol, ergosterol peroxide, cerevisterol, have been identified by the characteristic MS-spectra and co-TLC.…”

Section: Restrlts and Discussionmentioning

confidence: 99%

Investigation on Some Compounds Biosynthesized by Fruitbodies of Naematoloma Fasciculare/Huds. Ex Fr./P. Karst

Diak¹

1977

Planta Med

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The chromatographic analysis of ethanolic extract from N a e m a t o 1 o m a f a s c i c u 1 a r e fruitbodies indicated 20 nitrogen compounds (4 liquid amines, 4 volatile amines, 10 amino acids, 2 purines) 5 sugars, 4 sterols. Ergosterol, ergosterol peroxide, cerevisterol were separated by column chromatography and crystallized.Naematoloma fasciculare HUDS. ex Fr. P. KARST* a representative of xylophilous Basidiomycetes beIongs to the family Strophariaceae [9, 171. Ethanolic extract of N. fasciculare shows diuretic and parasymphathetic action in rats after ip administration [15]. Herbich et al. [6] reported that the fatal poisonings of men with fruitbodies of N. fasciculare were connected with necrosis of the liver, damage of the cardiac muscle and brain cells. The previously described*:-investigations on mycelial cultures (surface and submerged) obtained from the explantats of N. fasciculare fruitbodies and analyzed compounds biosynthesized in vitro.The aim of the present study was a phytochemical analysis of the constituents occuring in ethanolic extract of N. fasciculare fruitbodies collected in the natural habitats. ExperimentalGeneral: The infrared spectra were taken in KBr pellets on a Digilap. Mod. FTS-20 spectrometer. The mass spectra were measured with a LKB 9000s in the Regional Laboratory of Physicochemical Analysis and Structural Research in Krak6w. The melting points were determined on a Boetius hot stage microscope and are uncorrected. * synonym: Hypholorna fasciculare (FR.) QUEL. :' * J. DIAK: POI.Abreviations used: Be = benzene, n-BuOH = n-butanol, EtOAc = ethyl acetate, He = heksane, HOAc = acetic acid, M,Co = acetone, MeCOEt = ethylmethyl ketone, MeOH = methanol, PhOH = phenol, iso-PrOH = iso-propanol, Pyr = pyridine.Plant material: The well developed (open hats) fruitbodies of N. fasciculare were collected in the natural habitats in 1973-1975.Extraction methods: The fresh fruitbodies were washed in runnig water and homogenized with ethanol. After centrifugation of the precipitate, ethanolic extract was analyzed acc. to the scheme in Fig. 1.Paper chromatography: For separation of nitrogen compounds and sugars,

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The action of perphthalic acid on 5-dihydroergosteryl and ergosteryl acetates

Cited by 22 publications

References 0 publications

New Sterols and Triterpenoids from Four Edible Mushrooms.

New Sterols and Triterpenoids from Four Edible Mushrooms.

Fungal Metabolites. VIII: Structures of New Sesquiterpenes From Lactarius Scrobiculatus

Investigation on Some Compounds Biosynthesized by Fruitbodies of Naematoloma Fasciculare/Huds. Ex Fr./P. Karst

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